Borane;tetrahydrofuran → HCID 54350117, compound

HRID 487316Notes

Reaction equation

HRID 487316 reaction equation
B.C1COCC1.Cl.[CH3:8][C@H:9]1[N:14]([CH2:15][CH2:16][NH:17][C:18](=O)[C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)[C@@H:13]([CH3:29])[C:12]2[S:30][CH:31]=[CH:32][C:11]=2[CH2:10]1>>[CH3:8][C@H:9]1[N:14]([CH2:15][CH2:16][NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)[C@@H:13]([CH3:29])[C:12]2[S:30][CH:31]=[CH:32][C:11]=2[CH2:10]1

Participants

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 67850753HCID 67850753, compound

Product 1

HCID 54350117HCID 54350117, compoundYield 58.3%

Procedure

A borane/THF (48 ml, 48 mmol) solution of the amide from Example 28 (3.50 g, 9.74 mmol) was stirred at reflux for 12 hours under nitrogen. After the solution was quenched with 6N HCl, the THF was removed in vacuo. The acidic residue was warmed on a steambath for 15-20 min and then it was treated with 50% NaOH to afford a pH of 10. The aqueous mixture was extracted with CH2Cl2 and the combined extract was washed with brine and dried (Na2SO4). Solvent removal produced the crude product that was purified by flash silica gel column chromatography using 0.5-4% MeOH in CH2Cl2. There was obtained 1.96 g (58%) of the title compound that was treated with oxalic acid (1.1 eq) in acetone to produce a tan solid: mp 211°- 213° C.; IR (KBr) 3040, 2840, 1720, 1625, 1520, 1345, 1210, 855, 715 and 700 cm-1.

Workup

  1. temperatureat reflux for 12 hours under nitrogen
  2. customAfter the solution was quenched with 6N HCl
  3. customthe THF was removed in vacuo
  4. temperatureThe acidic residue was warmed on a steambath for 15-20 min
  5. additionit was treated with 50% NaOH
  6. customto afford a pH of 10
  7. extractionThe aqueous mixture was extracted with CH2Cl2
  8. extractionthe combined extract
  9. washwas washed with brine
  10. dry with materialdried (Na2SO4)
  11. customSolvent removal
  12. customproduced the crude product that
  13. customwas purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-f82e88578f904346aa79bf012250c2f9
Source dataset
uspto-grants-1994_03
Patent number
US05294621

Reaction notes

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